361519-96-2

Upstream product

• 248948-53-0 (αS,3S)-3-[[(1,1-dimethylethoxy)carbonyl]methylamino]-α-[(4-methoxyphenyl)methyl]-2,8-dioxo-1-azaspiro[4,5]decane-1-acetaldehyde 
• 333999-57-8 (1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.0^1,5]dodecan-4,9-dione 
• 58559-09-4 Ethyl N-(p-tosyl)tyrosinate 
• 333999-55-6 (3S,1S')-1-[2'-hydroxy-1'-(4-methoxybenzyl)-ethyl]-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-1-azaspiro[4.5]decan-2,8-dione 
• 333999-52-3 (3S,1S')-1-[2'-acetoxy-1'-(4-methoxybenzyl)-ethyl]-3-[N-acetyl-N-(4-methylphenyl)sulfonylamino]-1-azaspiro[4.5]deca-6,9-dien-2,8-dione 
• 333999-53-4 (3S,1S')-1-[2'-acetoxy-1'-(4-methoxybenzyl)-ethyl]-3-[N-acetyl-N-(4-methylphenyl)sulfonylamino]-1-azaspiro[4.5]decan-2,8-dione 
• 1395687-54-3 (R)-1-allyl-5-(benzyloxy)piperidin-2-one 
• 1395687-62-3 (2R,5R)-2-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-5-(benzyloxy)-2-vinylpiperidine 
• 1395687-70-3 (3R,6R)-6-[2-(1,3-dioxolan-2-yl)ethyl]-1-allyl-6-vinylpiperidin-3-ol 
• 1395687-78-1 C₁₅H₂₃NO₃ 
• 1254985-48-2 (R)-1-allyl-3-benzyloxy-2,6-piperidinedione 
• 1395687-85-0 (1S,5S,6R)-2-allyl-1-vinyl-2-azaspiro[bicyclo[3.3.1]nonane-4,2′-[1,3]dioxolan]-6-ol 
• 1416404-25-5 (1S,5S,6R)-2-allyl-6-(tert-butyldimethylsilyloxy)-1-vinyl-2-azaspiro{bicyclo[3.3.1]nonane-4,2′-[1,3]dioxolane} 
• 1395687-93-0 C₂₂H₂₉NO₃ 

Downstream Products

• 248948-70-1 (2S,5S,6S,7S,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]-6-(triethylsilyloxy)octahydro-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-ol 
• 248948-67-6 (2S,5S,6S,7S,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]-6-(triethylsilyloxy)octahydro-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl acetate 
• 248948-63-2 (2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate 
• 248948-75-6 (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate 
• 248948-65-4 (2S,5S,6S,7R,8R,10aS)-2-[[(benzyloxy)carbonyl]methylamino]-6-(triethylsilyloxy)octahydro-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl (4-nitrobenzene)sulfonate 
• 248948-72-3 (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]-6-(triethylsilyloxy)octahydro-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate 
• 1416404-33-5 C₂₀H₃₁N₂O₆P*ClH 
• 361519-97-3 Phosphoric acid dibenzyl ester (1S,3S,6S,7S,8R,9S)-7-hydroxy-6-(4-methoxy-benzyl)-3-methylamino-5-aza-tricyclo[6.3.1.0^1,5]dodec-9-yl ester 

Relevant academic research and scientific papers

Enantioselective total syntheses of (-)-FR901483 and (+)-8- epi -FR901483

The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

Total synthesis of tricyclic azaspirane derivatives of tyrosine: FR901483 and TAN1251C

A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.

Total Synthesis of (-)-FR901483

The first synthesis of the immunosuppressant (-)-FR901483 (1) has been accomplished in 2% overall yield from O-methyltyrosine methyl ester (31) in 22 steps establishing the absolute stereochemistry of the natural product. A 1,3-dipolar cycloaddition of ni